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Hydrochloric Acid → HCID 178490721, compound

HRID 1360242
Notes
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Reaction equation

HRID 1360242 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH:13]=[CH:14][C:15]3[O:20][CH2:19][CH2:18][N:17]([S:21]([C:24]4[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=4[O:31][CH3:32])(=[O:23])=[O:22])[C:16]=3[CH:33]=2)=[O:11])=[CH:5][CH:4]=1)#[N:2].[Cl-].[NH4+].[N-:36]=[N+:37]=[N-:38].[Na+].Cl>CN(C)C=O>[NH:36]1[C:1]([C:3]2[CH:4]=[CH:5][C:6]([NH:9][C:10]([C:12]3[CH:13]=[CH:14][C:15]4[O:20][CH2:19][CH2:18][N:17]([S:21]([C:24]5[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=5[O:31][CH3:32])(=[O:23])=[O:22])[C:16]=4[CH:33]=3)=[O:11])=[CH:7][CH:8]=2)=[N:2][N:38]=[N:37]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 667886204-(5-chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid (4-cyano-phenyl)-amide

Product 1

HCID 178490721HCID 178490721, compound

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

A microwave tube was charged with a solution of 4-(5-chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid (4-cyano-phenyl)-amide (50 mg, 0.10 mmol) in dimethylformamide (2.0 mL). Ammonium chloride (102 mg, 1.9 mmol) and sodium azide (121 mg, 1.9 mmol) were added and the tube was sealed under an argon atmosphere and irradiated in a microwave oven at a temperature of 155° C. for 35 min. The mixture was then acidified with HCl 1N and extracted three times with ethyl acetate. The combined organic extracts were dried over sodium sulfate and evaporated. The crude was resuspended in dichloromethane and sonicated. Filtration yielded 4-(5-chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid [4-(1H-tetrazol-5-yl)-phenyl]-amide as a white solid, 35 mg (64%), MS (ISP): m/e=525.0, 527.0 (M−H).

Workup

  1. customthe tube was sealed under an argon atmosphere
  2. customirradiated in a microwave oven at a temperature of 155° C. for 35 min
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. customevaporated
  6. customsonicated
  7. filtrationFiltration

Sources & evidence

ORD record
ord-7c3a2605921344159906eb7c96f2c632
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07879845B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes